Preparation of aromatic carbonyl or sulfonyl compounds with an aryl ether structure

Abstract

A process for the preparation of aromatic carbonyl or sulfonyl compounds with a diaryl ether structure by reacting phenols with halogenated carbonyl- or sulfonylaromatic compounds in a dipolar aprotic solvent is carried out in the presence of catalytic amounts of alkali metal nitrite or an aromatic nitro, nitroso, azo, azoxy or hydrazo compound.

We claim: 
     
       1. A process for preparing an aryl ether of the formula I ##STR20## wherein the ring A is unsubstituted, substituted or benzo-fused; X is carbonyl or sulfonyl;   L is a chemical bond or a linking group; and i) when L is a linking group, Y 1  is halogen or a radical of the formula ##STR21##  where n is 0 or 1 and X and the ring A have the abovementioned meanings; ii) when L is a chemical bond and X is carbonyl, Y 1  is hydrogen, C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy or a radical of the formula ##STR22##  where the ring A has the above-mentioned meansings; or iii) when L is a chemical bond and X is sulfonyl, Y 1  is a radical of the formula ##STR23## where the ring A has the above-mentioned meanings,, comprising: reacting a phenol of the formula II ##STR24## where the ring A has the above-mentioned meanings, with a halogen compound of the formula III ##STR25##  wherein Hal is chlorine or bromine;     L is a chemical bond or a linking group; and   Y 2  is a radical of the formula ##STR26##  wherein when L is a linking group, Y 2  is a radical of the formula ##STR27##  or the above-mentioned radical Y 1 , wherein i) when L is a linking group, Y 1  is halogen or a radical of the formula ##STR28##  where n is 0 or 1 and X and the ring A have the above-mentioned meansings;   ii) when L is a chemical bond and X is carbonyl, Y 1  is hydrogen, C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy or a radical of the formula ##STR29##  where the ring A has the above-mentioned meanings; or iii) when L is a chemical bond and X is sulfonyl, Y 1  is a radical of the formula ##STR30##  where the ring A has the above-mentioned meanings, where X, Hal and the ring A each have the above-mentioned meanings,    in a dipolar aprotic solvent in the presence of a base, at a reaction temperature of from 60° to 240° C., in the presence of a catalytically effective amount of a compound selected from the group consisting of an alkali metal nitrite compound, a compound of the formula IV ##STR31##  and a mixture thereof; wherein R 1  and R 2  are identical or different and each independently is hydrogen, C 1  -C 12  -alkyl which is unsubstituted or substituted by phenyl, or is C 1  -C 12  -alkoxy, halogen or nitro, and     R 3  is nitro, nitroso, or a radical of the formula ##STR32##  where R 4  is hydrogen, C 1  -C 4  -alkyl or halogen and Z is a radical of the formula --N═N, ##STR33##  or --NH--NH--, with the proviso that when R 3  is nitro, at least one of the two radicals R 1  and R 2  is halogen.   
     
     
       2. A process as claimed in claim 1, wherein the ring A is unsubstituted, is substituted by phenyl or is benzo-fused. 
     
     
       3. A process as claimed in claim 1, wherein L is a linking group. 
     
     
       4. A process as claimed in claim 1, wherein Hal is chlorine. 
     
     
       5. A process as claimed in claim 1, wherein aryl ethers of the formula Ia ##STR34## where the ring A is unsubstituted, is substituted by phenyl or is benzo-fused, X is carbonyl or sulfonyl,   L is phenylene or biphenylylene and   n is 0 or 1, are prepared by reacting phenols of the formula II ##STR35## where the ring A has the abovementioned meanings, with halogen compounds of the formula IIIa ##STR36## where X, L and n each have the abovementioned meanings.   
     
     
       6. A process as claimed in claim 1, wherein the reaction is carried out in the presence of a compound of the formula IV.